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Compounds

COMPOUND NPA010784

STRUCTURE
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PROPERTIES
NPAID NPA010784
CLUSTER ID 193
NODE ID 181
NAME Stephacidin A
FORMULA C26H29N3O3
MOLECULAR WEIGHT (Da) 431.5360
ACCURATE MASS (Da) 431.2209
ORIGIN ORGANISM TYPE Fungus
ORIGIN GENUS Aspergillus
ORIGIN SPECIES ochraceus
InChIKey YCWBTRJVYADFLQ-IMDCKVJKSA-N
InChI InChI=1S/C26H29N3O3/c1-23(2)10-8-15-17(32-23)7-6-14-16-12-26-18(24(3,4)20(16)27-19(14)15)13-25(21(30)28-26)9-5-11-29(25)22(26)31/h6-8,10,18,27H,5,9,11-13H2,1-4H3,(H,28,30)/t18-,25+,26-/m0/s1
SMILES CC1(C)C=CC2=C(C=CC3=C2NC2=C3C[C@@]34NC(=O)[C@@]5(CCCN5C3=O)C[C@H]4C2(C)C)O1
ORIGINAL ISOLATION REFERENCE
CITATION Qian-Cutrone, Jingfang; Huang, Stella; Shu, Yue-Zhong; Vyas, Dolatrai; Fairchild, Craig; Menendez, Ana; Krampitz, Kimberly; Dalterio, Richard; Klohr, Steven E.; Gaot, Qi Stephacidin A and B: Two structurally novel, selective inhibitors of the testosterone-dependent prostate LNCaP cells Journal of the American Chemical Society 2002 124 (49) 14556-14557.
DOI 10.1021/ja028538n PMID 12465964
ORIGINAL ISOLATION TAXONOMY
RANK NAME DB LINK NCBI
Domain Eukarya - 2759
Kingdom Fungi MycoBank 4751
Phylum Ascomycota MycoBank 4890
Class Eurotiomycetes MycoBank 147545
Order Eurotiales MycoBank 5042
Family Aspergillaceae MycoBank 1131492
Genus Aspergillus MycoBank 5052
SYNTHESES
CITATION 1 Greshock TJ; Grubbs AW; Jiao P; Wicklow DT; Gloer JB; Williams RM Isolation, structure elucidation, and biomimetic total synthesis of versicolamide B, and the isolation of antipodal (-)-stephacidin A and (+)-notoamide B from Aspergillus versicolor NRRL 35600. Angewandte Chemie International Edition 2008 47 (19) 3573-3577. DOI: 10.1002/anie.200800106 PMID: 18389509
CITATION 2 Baran PS; Guerrero CA; Ambhaikar NB; Hafensteiner BD Short, enantioselective total synthesis of stephacidin A. Angewandte Chemie International Edition 2005 44 (4) 606-609. DOI: 10.1002/anie.200461864 PMID: 15586393
CITATION 3 Greshock TJ; Grubbs AW; Tsukamoto S; Williams RM A concise, biomimetic total synthesis of stephacidin A and notoamide B. Angewandte Chemie International Edition 2007 46 (13) 2262-2265. DOI: 10.1002/anie.200604378 PMID: 17304610
CITATION 4 Sunderhaus JD; McAfoos TJ; Finefield JM; Kato H; Li S; Tsukamoto S; Sherman DH; Williams RM Synthesis and bioconversions of notoamide T: a biosynthetic precursor to stephacidin A and notoamide B. Organic Letters 2013 15 (1) 22-25. DOI: 10.1021/ol302901p PMID: 23249380
CITATION 5 Greshock TJ; Williams RM Improved biomimetic total synthesis of D,L-stephacidin A. Organic Letters 2007 9 (21) 4255-4258. DOI: 10.1021/ol701845t PMID: 17854197
CITATION 6 Artman GD; Grubbs AW; Williams RM Concise, asymmetric, stereocontrolled total synthesis of stephacidins A, B and notoamide B. Journal of the American Chemical Society 2007 129 (19) 6336-42. DOI: 10.1021/ja070259i PMID: 17455936
REVISIONS
VERSION SMILES CITATION
Original Isolation CC1(C=CC2=C(O1)C=CC3=C2NC4=C3CC56C(C4(C)C)CC7(CCCN7C5=O)C(=O)N6)C Qian-Cutrone, Jingfang; Huang, Stella; Shu, Yue-Zhong; Vyas, Dolatrai; Fairchild, Craig; Menendez, Ana; Krampitz, Kimberly; Dalterio, Richard; Klohr, Steven E.; Gaot, Qi Stephacidin A and B: Two structurally novel, selective inhibitors of the testosterone-dependent prostate LNCaP cells Journal of the American Chemical Society 2002 124 (49) 14556-14557. DOI: 10.1021/ja028538n PMID: 12465964
2 CC1(C)C=CC2=C(C=CC3=C2NC2=C3C[C@@]34NC(=O)[C@@]5(CCCN5C3=O)C[C@H]4C2(C)C)O1 Baran, Phil S; Hafensteiner, Benjamin D; Ambhaikar, Narendra B; Guerrero, Carlos A; Gallagher, John D Enantioselective total synthesis of avrainvillamide and the stephacidins. Journal of the American Chemical Society 2006 128 (26) 8678-93. DOI: 10.1021/ja061660s PMID: 16802835
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